1885-23-0

Usage

Uses

Used in Riot Control:
Dibromomalononitrile is used as a riot control agent, causing severe eye, skin, and respiratory irritation. Its potent effects make it a deterrent in crowd control situations.
Used in Chemical Warfare:
Due to its toxicity, dibromomalononitrile has been used as a chemical warfare agent, although its use is strictly regulated and controlled.
Used in Dye Production:
Dibromomalononitrile is used in the production of some types of dyes, but its application in this industry is limited due to its hazardous nature.
Used in Pharmaceutical Industry:
dibromomalononitrile is also utilized in the production of certain pharmaceuticals, albeit with strict control measures in place to mitigate its potential risks.
Regulation:
Due to its toxicity and potential for misuse, dibromomalononitrile is classified as a Schedule 3 substance under the Chemical Weapons Convention, ensuring that its production, use, and trade are subject to stringent international oversight.

InChI:InChI=1/C3Br2N2/c4-3(5,1-6)2-7

Upstream product

• 109-77-3 malononitrile 
• 7732-18-5 water 
• 7726-95-6 bromine 

Downstream Products

• 4354-73-8 2-(cyclohexylidene)malononitrile 
• 670-54-2 ethenetetracarbonitrile 
• 10222-01-2 2,2-dibromo-3-nitrilopropionamide 
• 586-77-6 4-bromo-N,N-dimethylaniline 
• 1885-22-9 bromomalononitrile 
• 72228-00-3 1,5-Dibrom-1,5-diphenyl-3,3-dicyan-pentan 
• 1885-26-3 2-(2-bromo-2-phenylethyl)malononitrile 
• 22984-59-4 4-Hydroxy-4-phenyl-1-carboxy-buttersaeure 
• 90562-12-2 (2-Brom-cyclohexyl)-brommalonsaeure-dinitril 
• 6904-17-2 1,1-dicyano-2-phenylcyclopropane 
• 23767-79-5 3-phenylcyclopropane-1,1,2,2-tetracarbonitrile 
• 77526-58-0 Cyanodibromoacetyliminotriphenylarsorane 
• 80232-77-5 C₂₉H₁₉Br₂N₄O₂P 
• 90418-91-0 3-ethyl-1,1,2,2-tetracyanopropane 

Relevant academic research and scientific papers

Chemical reactivity of 3-hydrazino-5,6-diphenyl-1,2,4-triazine towards π-acceptors activated carbonitriles

Behaviour of 3-hydrazino-5,6-diphenyl-1,2,4-triazine 1 as electron donor towards different electron acceptors activated carbonitriles has been investigated and a novel fused heterocyclic system and 2,3-disubstituted 1,2,4-triazines have been obtained. Compound 1 reacts with 1,2-dicyanobenzene as π-acceptor in DMF to form benzencarboximidamide 16, while reaction of 1 with a-bromomalononitrile 17 in boiling DMF affords compound 18. On the other hand, compound 1 reacts with tetracyanoethane 23 in DMF to yield compound 24. The route of reaction in DMF indicates that charge-transfer complexation is the key intermediate to obtain new heterocyclic systems. Structures of the products are established by MS, IR, UV-Vis, CHN and 1H NMR spectral data.

!,3-Dipolar cycloaddition of α-phenyl-N-tert-butylnitrone (PBN) to dichloro- and dibromo-malononitrile, chlorotricyanomethane and tetracyanomethane. Structure of products and kinetics of their formation

The kinetics of cycloaddition between α-phenyl-N-tert-butylnitrone (PBN, IUPAC name: N-benzylidene-tert-butylamine N-oxide) and six activated nitriles R-CN, viz. dibromo- and dichloro-malononitrile (1a and 1b), chlorotricyanomethane (1c), tetracyanomethane (1d), trichloroacetonitrile (1e) and carbamoylchlorodicyanomethane (5), to give 2-tert-butyl-3-phenyl-5-R-2,3-dihydro-1,2,4-oxadiazoles 2a-e have been determined, as well as the similar reaction between 4-NO2PBN and 1c.The second-order rate constants for reaction between PBN and 1 in acetonitrile fall (relative rate constant in parenthesis) in the order of 1d (5.4*103) > 1c (3.1*102) > 1b (8) > 5 (not given) > 1e (9*10-3).The rate constants are slightly larger in non-polar solvents.The rate constants of the PNB-1c and PNB-1d cycloadditions (0.15 and 2.6 dm3 mol-1 s-1, respectively) are of the same magnitude as those recently used to classify thioketones as 'superdipolarophiles'.X-Ray crystal structures are reported for 2-tert-butyl-3-phenyl-5-(dichlorocyanomethyl)-2,3-dihydro-1,2,4-oxadiazole (2b) and 2-tert-butyl-3-phenyl-5-(chlorodicyanomethyl)-2,3-dihydro-1,2,4-oxadiazole (2c).